title: Structures and absolute configurations of penicillactones A-C from an endophytic microorganism, Penicillium dangeardii Pitt.
abstract: Penicillactones A-C (1-3) are structurally related natural products with a spirocyclic anhydride structure and were isolated from the endophytic fungus Penicillium dangeardii Pitt. Penicillactones B and C showed inhibition of the release of β-glucuronidase from polymorphonuclear leukocytes with ED50 values of 2.58 and 1.57 μM. A 2D INADEQUATE experiment of 1 was performed at natural abundance to confirm the arrangement of its carbon skeleton. The configurations of 1-3 were established through extensive NMR spectroscopic analysis, selective structural modifications, and CD analysis.
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College , Beijing 100050, China , Department of Chemical and Biomolecular Engineering, Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
authors.forename: Yunbao
authors.initials: Y
authors.lastname: Liu
authors.forename: Guangzhi
authors.initials: G
authors.lastname: Ding
authors.forename: Yong
authors.initials: Y
authors.lastname: Li
authors.forename: Jing
authors.initials: J
authors.lastname: Qu
authors.forename: Shuanggang
authors.initials: S
authors.lastname: Ma
authors.forename: Haining
authors.initials: H
authors.lastname: Lv
authors.forename: Yang
authors.initials: Y
authors.lastname: Liu
authors.forename: Wenjie
authors.initials: W
authors.lastname: Wang
authors.forename: Jungui
authors.initials: J
authors.lastname: Dai
authors.forename: Yi
authors.initials: Y
authors.lastname: Tang
authors.forename: Shishan
authors.initials: S
authors.lastname: Yu
mesh_terms: D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D005966:Glucuronidase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D006801:Humans; D007783:Lactones / Q000737:chemistry* / Q000302:isolation & purification; D008958:Models, Molecular; D015394:Molecular Structure; D009504:Neutrophils / Q000201:enzymology / Q000378:metabolism; D010407:Penicillium / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry* / Q000302:isolation & purification; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D004791:Enzyme Inhibitors; D007783:Lactones; D013141:Spiro Compounds; C587559:penicillactone A; C587560:penicillactone B; C587561:penicillactone C; D005966:Glucuronidase